CN105399758A - Annular chiral coordination polymer, a preparation method and applications - Google Patents
Annular chiral coordination polymer, a preparation method and applications Download PDFInfo
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- CN105399758A CN105399758A CN201510929259.9A CN201510929259A CN105399758A CN 105399758 A CN105399758 A CN 105399758A CN 201510929259 A CN201510929259 A CN 201510929259A CN 105399758 A CN105399758 A CN 105399758A
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- ligand polymer
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- 238000002360 preparation method Methods 0.000 title abstract description 12
- 229920001795 coordination polymer Polymers 0.000 title abstract 5
- 239000013256 coordination polymer Substances 0.000 title abstract 5
- 239000003446 ligand Substances 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000000725 suspension Substances 0.000 claims abstract description 14
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 8
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 38
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 6
- -1 polytetrafluoroethylene Polymers 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000013110 organic ligand Substances 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 235000019587 texture Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006842 Henry reaction Methods 0.000 abstract 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
- B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an annular chiral coordination polymer, a preparation method and applications. The chemical formula is [Cu3(R,R-cdpa)3(CH3OH)3].6ClO4.3CH3OH. The preparation method comprises steps: Cu(ClO4)2.6H2O and R,R-cdpa are added in 8mL of a CH3OH solution, mixing is carried out, and a suspension is prepared; the suspension is transferred to a reaction vessel, the reaction is carried out, and an annular chiral coordination polymer is prepared. The preparation method is advantageous in that the bichelating ligand R,R-cdpa based on chiral cyclohexanediamine and and Cu(II) are employed to prepare an annular chiral coordination polymer. In addition, the preparation technology is simple, complex synthesis devices are not needed, and the production cost is lowered. the prepared coordination polymer can be used in an asymmetric Henry reaction of aromatic aldehyde and nitromethane.
Description
Technical field
The invention belongs to chemical field, particularly relate to a kind of cyclic chiral ligand polymer and preparation method thereof and application.
Background technology
The design of chiral coordination compound and synthesis are one of hot fields of coordination chemistry, this is because their structure is full of variety, colourful topological framework can be shown, therefore not only there is the theoretical significance of structure, can be used as excellent functional materials simultaneously, there is tempting application prospect.Research at present for this material mainly concentrates on asymmetry catalysis, enantioselectivity separation, second-order non-linear optical materials and ferroelectric material etc.In recent years, lot of domestic and international seminar has made a large amount of fruitful work in the asymmetry catalysis of chiral coordination compound, but mainly concentrate on the ligand polymer of higher dimensionality (two and three dimensions), particularly there is the metal-organic framework materials of pore passage structure.Meanwhile, cyclic chiral ligand polymer, as a kind of interesting chipal compounds, also should have potential using value in asymmetry catalysis, but does not also have the research of this respect to report in document.In addition, in document, the adducts of existing chirality cyclohexanediamine and Cu (II) salt is applied in the report of asymmetric Henle reaction aspect.
Summary of the invention
Goal of the invention: that the first object of the present invention is to provide a kind of one dimension and there is the chirality ligand polymer of ring-type; The second object of the present invention is to provide the preparation method of this ligand polymer; The third object of the present invention is to provide the application of this ligand polymer.
Technical scheme: the chemical formula of cyclic chiral ligand polymer of the present invention is [Cu
3(R, R-cdpa)
3(CH
3oH)
3] .6ClO
4.3CH
3oH, wherein, R, R-cdpa are that it is the two chelated organic ligands of chirality.Furtherly, what this ligand polymer had that three Cu (II) and three R, R-cdpa formed 3 adds 3 ring texturees, and it belongs to oblique system, and spacer is P2
1, crystallization parameters is
β=99.128 (3) °,
wherein, the rib that a, b, c are respectively three ribs of structure cell is long, and β is the angle of a rib and c rib.
Furtherly, R of the present invention, R-cdpa part adopts trans pair of chelating pattern and the coordination of two Cu (II), and the tetragonal pyramid structure that Cu (II) is pentacoordinate, the base plane of tetragonal pyramid is occupied by two nitrogen-atoms of two chelating ligands and two Sauerstoffatoms, and the vertex position of tetragonal pyramid is occupied by a water molecules, bottom tetragonal pyramid, four atoms of coordination are not in same plane, wherein, the structural formula of R, R-cdpa part is:
The preparation method of cyclic chiral ligand polymer of the present invention comprises the steps:
(1) by the Cu (ClO of 0.1mmol
4)
26H
2the R of O and 0.1mmol, R-cdpa adds 8mLCH
3mix in OH solution, stirred at ambient temperature 20min, obtains suspension liquid;
(2) above-mentioned suspension transferred in the reactor of 15mL inner liner polytetrafluoroethylene and heat 90 DEG C of reactions after 3 days, be slowly down to room temperature, filtration with the speed of 5 DEG C/h, leave standstill rear obtained cyclic chiral ligand polymer.
Cyclic chiral ligand polymer of the present invention is applied to the asymmetric Henle reaction of aromatic aldehyde and Nitromethane 99Min..
Beneficial effect: compared with prior art, its remarkable advantage is that the present invention adopts two chelating ligand R, R-cdpa and Cu (II) based on chirality cyclohexanediamine to construct a kind of cyclic chiral ligand polymer; Meanwhile, preparation technology of the present invention is simple, without the need to the synthesis device of complexity, reduces production cost; In addition, the ligand polymer of preparation can be applied to the asymmetric Henle reaction of aromatic aldehyde and Nitromethane 99Min., thus explores and feasibility study for chiral helical title complex provides originality as the application of heterogeneous catalyst in asymmetry catalysis.
Accompanying drawing explanation
Fig. 1 is the molecular structure of the ligand polymer that the present invention obtains.
Embodiment
The chemical formula of cyclic chiral ligand polymer of the present invention is [Cu
3(R, R-cdpa)
3(CH
3oH)
3] .6ClO
4.3CH
3oH, wherein, R, R-cdpa are (-)-N, N'-(1R, 2R)-1,2-diamino hexahydroaniline two base two (2-pyridine anilide), and it be chirality pair chelated organic ligands.Furtherly, what this ligand polymer had that three Cu (II) and three R, R-cdpa formed 3 adds 3 ring texturees, and it belongs to oblique system, and spacer is P2
1, crystallization parameters is
β=99.128 (3) °,
wherein, the rib that a, b, c are respectively three ribs of structure cell is long, and β is the angle of a rib and c rib.
Furtherly, R of the present invention, R-cdpa part adopts trans pair of chelating pattern and the coordination of two Cu (II), and the tetragonal pyramid structure that Cu (II) is pentacoordinate, the base plane of tetragonal pyramid is occupied by two nitrogen-atoms of two chelating ligands and two Sauerstoffatoms, and the vertex position of tetragonal pyramid is occupied by a water molecules, bottom tetragonal pyramid, four atoms of coordination are not in same plane, wherein, the structural formula of R, R-cdpa part is:
The preparation method of cyclic chiral ligand polymer of the present invention comprises the steps:
(1) by the Cu (ClO of 0.1mmol
4)
26H
2the R of O and 0.1mmol, R-cdpa adds 8mLCH
3mix in OH solution, stirred at ambient temperature 20min, obtains suspension liquid;
(2) above-mentioned suspension transferred in the reactor of 15mL inner liner polytetrafluoroethylene and heat 90 DEG C of reactions after 3 days, be slowly down to room temperature, filtration with the speed of 5 DEG C/h, leave standstill rear obtained cyclic chiral ligand polymer.
Cyclic chiral ligand polymer of the present invention is applied to the asymmetric Henle reaction of aromatic aldehyde and Nitromethane 99Min..Furtherly, aromatic aldehyde is that (substituting group is H, 2-/3-/4-NO for 1-naphthaldehyde and single-substituted formaldehyde
2, 2-/3-/4-F, 2-/4-Cl, 2-/3-/4-Br, 4-OCH
3or 4-Ph).
Embodiment 1
By the Cu (ClO of 0.1mmol
4)
26H
2the R of O and 0.1mmol, R-cdpa adds 8mLCH
3mix in OH solution, stirred at ambient temperature 20min, obtains suspension liquid; Above-mentioned suspension is transferred in the reactor of 15mL inner liner polytetrafluoroethylene and heat 90 DEG C of reactions after 3 days, slowly be down to room temperature, filtration with the speed of 5 DEG C/h, leave standstill after obtained cyclic chiral ligand polymer, the molecular structure this ligand polymer obtained through Advances in crystal X-ray diffraction analysis is as shown in Figure 1.
Embodiment 2
By the Cu (ClO of 0.1mmol
4)
26H
2the R of O and 0.1mmol, R-cdpa adds 8mLCH
3mix in OH solution, stirred at ambient temperature 20min, obtains suspension liquid; Above-mentioned suspension transferred in the reactor of 15mL inner liner polytetrafluoroethylene and heat 90 DEG C of reactions after 3 days, be slowly down to room temperature, filtration with the speed of 5 DEG C/h, leave standstill rear obtained cyclic chiral ligand polymer.
Embodiment 3
0.5mmol ligand polymer is added in the small test tube of 4mL, 1mL Virahol (i-PrOH) and 5mmolN, N-diisopropylethylamine (DIPEA) obtains a blue suspension, then in suspension, the aromatic aldehyde of 0.5mmol and the Nitromethane 99Min. of 5mmol is added, test tube is put into low-temp reaction device, filter react 168h under-20 DEG C of conditions after, filtrate is crossed column purification, wherein, weighting agent is silica gel, moving phase is sherwood oil and the ethyl acetate mixed solvent of volume ratio 4:1, gained solution is concentrated, after vacuum-drying, namely catalysate is obtained, its catalyzed reaction equation is shown below.
By the high-performance liquid chromatogram determination e.e. value of the catalysate of gained with chiral column.Wherein, chiral column used and liquid-phase condition, and the e.e. value of products therefrom is as shown in table 1.
The e.e. value of table 1 catalysate
As shown in Table 1, when this chiral helical title complex is as Primary Catalysts, the asymmetric Henle reaction of aromatic aldehyde and Nitromethane 99Min. can obtain good asymmetry catalysis effect; It is likely applied in industrial reaction.
Claims (9)
1. a cyclic chiral ligand polymer, is characterized in that: the chemical formula of this ligand polymer is [Cu
3(R, R-cdpa)
3(CH
3oH)
3] .6ClO
4.3CH
3oH, wherein, R, R-cdpa are that it is the two chelated organic ligands of chirality.
2. cyclic chiral ligand polymer according to claim 1, is characterized in that: what described ligand polymer had that three Cu (II) and three R, R-cdpa formed 3 adds 3 ring texturees.
3. cyclic chiral ligand polymer according to claim 1, is characterized in that: described ligand polymer belongs to oblique system, spacer is P2
1.
4. cyclic chiral ligand polymer according to claim 1, is characterized in that: the crystallization parameters of described ligand polymer is
β=99.128 (3) °,
wherein, the rib that a, b, c are respectively three ribs of structure cell is long, and β is the angle of a rib and c rib.
5. cyclic chiral ligand polymer according to claim 1, is characterized in that: the structural formula of described R, R-cdpa part is:
6. cyclic chiral ligand polymer according to claim 5, is characterized in that: described R, R-cdpa part adopts trans pair of chelating pattern and the coordination of two Cu (II).
7. cyclic chiral ligand polymer according to claim 6, it is characterized in that: the tetragonal pyramid structure that described Cu (II) is pentacoordinate, the base plane of tetragonal pyramid is occupied by two nitrogen-atoms of two chelating ligands and two Sauerstoffatoms, the vertex position of tetragonal pyramid is occupied by a water molecules, and bottom tetragonal pyramid, four atoms of coordination are not in same plane.
8. prepare a method for cyclic chiral ligand polymer according to claim 1, it is characterized in that comprising the steps:
(1) by the Cu (ClO of 0.1mmol
4)
26H
2the R of O and 0.1mmol, R-cdpa adds 8mLCH
3mix in OH solution, stirred at ambient temperature 20min, obtains suspension liquid;
(2) above-mentioned suspension transferred in the reactor of 15mL inner liner polytetrafluoroethylene and heat 90 DEG C of reactions after 3 days, be slowly down to room temperature, filtration with the speed of 5 DEG C/h, leave standstill rear obtained cyclic chiral ligand polymer.
9. a cyclic chiral ligand polymer according to claim 1 is applied to the asymmetric Henle reaction of aromatic aldehyde and Nitromethane 99Min..
Priority Applications (1)
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|---|---|---|---|
| CN201510929259.9A CN105399758A (en) | 2015-12-14 | 2015-12-14 | Annular chiral coordination polymer, a preparation method and applications |
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|---|---|---|---|
| CN201510929259.9A CN105399758A (en) | 2015-12-14 | 2015-12-14 | Annular chiral coordination polymer, a preparation method and applications |
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|---|---|
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Family
ID=55465555
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503737A (en) * | 2018-11-19 | 2019-03-22 | 石家庄学院 | A kind of polystyrene-supported chiral diamine class ligand and its preparation method and application |
| CN110560173A (en) * | 2019-09-17 | 2019-12-13 | 哈尔滨工业大学 | preparation method and application method of bipyridine amide iron-loaded nano silica heterogeneous catalyst |
-
2015
- 2015-12-14 CN CN201510929259.9A patent/CN105399758A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 曹青娜: "具有多重手性元素的手性配位聚合物的合成、结构与性质研究", 《HTTP://WWW.DOCIN.COM/P-1141639302.HTML》 * |
| 程林 等: "手性[3+3]金属环的构筑及其在不对称亨利反应中的应用", 《2015年中西部地区无机化学化工学术研讨会会议论文集》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503737A (en) * | 2018-11-19 | 2019-03-22 | 石家庄学院 | A kind of polystyrene-supported chiral diamine class ligand and its preparation method and application |
| CN109503737B (en) * | 2018-11-19 | 2021-03-05 | 石家庄学院 | Polystyrene-immobilized chiral diamine ligand and preparation method and application thereof |
| CN110560173A (en) * | 2019-09-17 | 2019-12-13 | 哈尔滨工业大学 | preparation method and application method of bipyridine amide iron-loaded nano silica heterogeneous catalyst |
| CN110560173B (en) * | 2019-09-17 | 2022-03-04 | 哈尔滨工业大学 | Preparation method and application method of bipyridine amide iron-loaded nano silica heterogeneous catalyst |
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Application publication date: 20160316 |